Reaction #1379889

Reaction equation

sodium hydroxide

product

4-(quinolin-5-ylamino)-benzoic Acid Methyl Ester

→

orange powder

4-(quinolin-5-ylamino)-benzoic Acid

Solvents

water

tetrahydrofuran

methanol

Conditions

Workup

1. 1
   Otherwas removed under reduced pressure
2. 2
   OtherThe resultant residue was purified
3. 3
   workup.DISSOLUTIONby dissolving in water (1000 ml)
4. 4
   Otherprecipitating the crude product by acidification to pH3 with 2N HCl
5. 5
   OtherThe precipitate so formed
6. 6
   Filtrationwas collected by filtration
7. 7
   Washwashed with water (250 ml)
8. 8
   OtherThis purification procedure
9. 9
   Otherwas dried

Procedure

A solution of sodium hydroxide (7 g, 0.18 mol) in water (100 ml) was added to a solution of the product from stage (a) in a mixture of tetrahydrofuran (100 ml) and methanol (350 ml). The reaction mixture was stirred at 50° C. for 3 h before the solvent was removed under reduced pressure. The resultant residue was purified by dissolving in water (1000 ml) adjusted to pH10 with 2M NaOH and precipitating the crude product by acidification to pH3 with 2N HCl. The precipitate so formed was collected by filtration and washed with water (250 ml). This purification procedure was repeated a further two times before the product was dried to give 12.3 g of an orange powder.

Source